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HOMA parameters for the boron–boron bond: How the introduction of a BB bond influences the aromaticity of selected hydrocarbons

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Abstract

An extension of the harmonic oscillator model of aromaticity (HOMA) model for systems with boron–boron bonds is presented. For the first time, the parameters of the HOMA model are estimated using only theoretically calculated bond lengths. The HOMA parameters obtained make geometric aromaticity studies possible for a large number of compounds containing the boron–boron bond. The derived HOMA parameters have been used to investigate how the introduction of the boron–boron moiety in the structure of selected hydrocarbons modifies their aromaticity. The conclusion is that the insertion of a boron–boron bond usually strongly decreases the aromaticity of the boron-containing compounds in comparison to their parent hydrocarbons.

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Acknowledgments

We thank Prof. Tadeusz M. Krygowski for his inspiration of our aromaticity research. We thank the Ministerio de Ciencia e Innovación (Project No. CTQ2009-13129-C02-02) and the Comunidad Autónoma de Madrid (Project MADRISOLAR2, ref. S2009/PPQ-1533) for their continuing support. Thanks are also given to ‘Cyfronet’ Krakow and to the CTI (CSIC) computer centres for an allocation of computer time.

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Authors and Affiliations

  1. Faculty of Chemistry, Jagiellonian University, 3 Ingardena Street, 30-060, Kraków, Poland

    Krzysztof K. Zborowski & Leonard M. Proniewicz

  2. Instituto de Química Médica (C.S.I.C.), Juan de la Cierva 3, 28006, Madrid, Spain

    Ibon Alkorta & Jose Elguero

  3. The State Higher Vocational School, Mickiewicza 8, 33-100, Tarnów, Poland

    Leonard M. Proniewicz

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  1. Krzysztof K. Zborowski
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  2. Ibon Alkorta
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  3. Jose Elguero
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  4. Leonard M. Proniewicz
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Correspondence to Krzysztof K. Zborowski.

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Zborowski, K.K., Alkorta, I., Elguero, J. et al. HOMA parameters for the boron–boron bond: How the introduction of a BB bond influences the aromaticity of selected hydrocarbons. Struct Chem 24, 543–548 (2013). https://doi.org/10.1007/s11224-012-0109-9

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  • DOI: https://doi.org/10.1007/s11224-012-0109-9

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